Artículos de revistas
Synthesis of tetrahydrofuran-based natural products and their carba analogs via stereoselective enzyme mediated Baeyer–Villiger oxidation
Fecha
2016-06Registro en:
Rudroff, Florian; Bianchi, Dario Alejandro; Moran Ramallal, Roberto; Iqbal, Naseem; Dreier, Dominik; et al.; Synthesis of tetrahydrofuran-based natural products and their carba analogs via stereoselective enzyme mediated Baeyer–Villiger oxidation; Pergamon-Elsevier Science Ltd; Tetrahedron; 72; 46; 6-2016; 7212-7221
0040-4020
CONICET Digital
CONICET
Autor
Rudroff, Florian
Bianchi, Dario Alejandro
Moran Ramallal, Roberto
Iqbal, Naseem
Dreier, Dominik
Mihovilovic, Marko D.
Resumen
In this work we present efficient formal syntheses of several biologically interesting natural products (showdomycin, goniofufurone, trans-kumausyne) and their novel carba analogs by applying different Baeyer–Villiger monooxygenases. This strategy provides access to tetrahydrofuran-based natural products, C-nucleosides and both antipodes of the corresponding carba analogs in high optical purities (up to >95% ee) starting from simple achiral and commercially available building blocks (tetrabromoacetone, furan and cyclopentadiene). The striking key features of this chemo-enzymatic approach are the introduction of four stereogenic centers in as few as three reaction steps within a desymmetrization approach and the short-cut of several reaction sequences by the implementation of a biocatalytic step.